tert-butyl 5-{[(benzyloxy)carbonyl]amino}pentanoate | 63983-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 5-{[(benzyloxy)carbonyl]amino}pentanoate
• 英文别名: tert-butyl 5-(phenylmethoxycarbonylamino)pentanoate
• CAS: 63983-88-0
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: VWLHJMBZIRZECB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-{[(benzyloxy)carbonyl]amino}pentanoate 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 magnesium sulfate 、 三乙胺 作用下， 以 甲醇 、 溶剂黄146 为溶剂， -5.0~25.0 ℃ 、413.69 kPa 条件下， 反应 5.5h， 生成 tert-butyl-5-(N-benzyl)aminopentanoate
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e
• 作为产物：
  描述：

  5-氨基颉草酸 在 吡啶 、 sodium hydroxide 、 三氯氧磷 作用下， 以 水 为溶剂， 生成 tert-butyl 5-{[(benzyloxy)carbonyl]amino}pentanoate
  参考文献：
  名称：

  Synthesis and Self-Association Properties of Flexible Guanidiniocarbonylpyrrole−Carboxylate Zwitterions in DMSO: Intra- versus Intermolecular Ion Pairing

  摘要：

  We have synthesized a new class of flexible zwitterions 6a-e, in which a carboxylate is linked via an alkyl chain with variable length (one to five methylene groups) to a guanidiniocarbonylpyrrole cation. The self-association properties of these zwitterions were determined by NMR dilution studies in DMSO and by ESI-MS experiments. The stability and hence also the size of the aggregates formed via self-assembly is critically dependent on the length and therefore flexibility of the spacer. Whereas the smallest zwitterion 6a forms large aggregates already at low concentrations, the more flexible zwitterions only form small oligomers (6b) or dimers (6c-e) at much larger concentrations. The differences between the five zwitterions can be explained based on the different extent of intramolecular ion pairing within the monomers. Any intramolecular ion pairing, which becomes possible with increasing linker length, stabilizes the monomer and therefore destabilizes any oligomer.

  DOI：

  10.1021/jo070641d

文献信息

• Antibacterial halogenoacetyl derivatives of amino acids and simple peptides
  作者：Jennifer Goodacre、Leonard Jeffries、John H. C. Nayler、Roger J. Ponsford、Irene Stirling

  DOI：10.1021/jm00221a015

  日期：1977.11

  amino acids. N-Iodoacetyl or -bromoacetyl derivatives of the peptides were then prepared in the hope that they would serve as active-site-directed irreversible inhibitors of cell wall transpeptidases. Certain of the halogenoacetyl dipeptide esters, but not the corresponding free acids, showed slight antistaphylococcal activity. Subsequent structural variation showed that inclusion of C-alanine or L-lysine

  D-丙氨酸和L-赖氨酸在细菌细胞壁中肽聚糖交联过程中的重要作用促使人们制备了包含这些氨基酸的各种小肽。然后制备肽的N-碘乙酰基或-溴乙酰基衍生物，希望它们可用作细胞壁转肽酶的活性位点导向的不可逆抑制剂。某些卤代乙酰二肽酯显示出轻微的抗葡萄球菌活性，但没有相应的游离酸。随后的结构变化表明，不需要包含C-丙氨酸或L-赖氨酸，因为当二肽单元被甘氨酰甘氨酸或ω-氨基链烷酸替代时，抗菌活性至少一样好。
• Optimized Reaction Pair of the CysHis Tag and Ni(II)-NTA Probe for Highly Selective Chemical Labeling of Membrane Proteins
  作者：Naoki Zenmyo、Hiroki Tokumaru、Shohei Uchinomiya、Hirokazu Fuchida、Shigekazu Tabata、Itaru Hamachi、Ryuichi Shigemoto、Akio Ojida

  DOI：10.1246/bcsj.20190034

  日期：2019.5.15

  Chemical labeling of proteins with synthetic molecular probes offers the possibility to probe the functions of proteins of interest in living cells. However, the methods for covalently labeling targeted proteins using complementary peptide tag-probe pairs are still limited, irrespective of the versatility of such pairs in biological research. Herein, we report the new CysHis tag-Ni(II) probe pair for the specific covalent labeling of proteins. A broad-range evaluation of the reactivity profiles of the probe and the CysHis peptide tag afforded a tag-probe pair with an optimized and high labeling selectivity and reactivity. In particular, the labeling specificity of this pair was notably improved compared to the previously reported one. This pair was successfully utilized for the fluorescence imaging of membrane proteins on the surfaces of living cells, demonstrating its potential utility in biological research.

  使用合成分子探针对蛋白质进行化学标记，提供了在活细胞中探测目标蛋白质功能的可能性。然而，尽管这种标记对生物研究非常灵活，利用互补肽标签-探针对共价标记目标蛋白的方法仍然有限。在此，我们报告了一种新的CysHis标签-Ni(II)探针对，用于特异性的共价标记蛋白质。对该探针和CysHis肽标签的反应性进行广泛评估，获得了一对优化后的高标记选择性和反应性的标签-探针对。特别是，与先前报道的标记对相比，这对的标记特异性显著提高。该对成功用于对活细胞表面膜蛋白的荧光成像，展示了其在生物研究中的潜在应用。
• [EN] SUBSTITUTED 2,3-BENZODIAZEPINES DERIVATIVES<br/>[FR] DÉRIVÉS DE 2,3-BENZODIAZÉPINES SUBSTITUÉS
  申请人：BAYER AG

  公开号：WO2021152113A1

  公开（公告）日：2021-08-05

  Derivatives of 2,3- benzodiazepines as inhibitors of Bromodomain and extra C-terminal domain (BET) proteins, in particular the BRD4 family member, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases for hyperproliferative disorders, in particular for tumor disorders. The 2,3- benzodiazepines derivatives according to the invention are active as inhibitors as well as degraders of BET proteins.

  2,3-苯二氮卓类衍生物作为溴结构域和额外C-末端结构域（BET）蛋白的抑制剂，特别是BRD4家族成员，用于制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及用于制造用于治疗或预防过度增殖疾病的药物组合物的所述化合物的使用，特别是用于肿瘤疾病。根据本发明的2,3-苯二氮卓类衍生物作为BET蛋白的抑制剂和降解剂。
• Substituierte 5-Amino-4-hydroxyvalerylderivate
  申请人：CIBA-GEIGY AG

  公开号：EP0143746A2

  公开（公告）日：1985-06-05

  Verbindungen der Formel worin R, Wasserstoff oder Acyl, X, einen gegebenenfalls N-alkylierten Aminosäurerest, der N-terminal mit R, und C-terminal mit X2 verbunden ist, X2 einen gegebenenfalls N-alkylierten Aminosäurerest, der N-terminal mit X, und C-terminal mit der Gruppe-NR2- verbunden ist, R2 Wasserstoff oder Niederalkyl, R3 Wasserstoff, Alkyl, Cycloalkyl, Arylniederalkyl oder Aryl, R4 Hydroxy oder veräthertes oder verestertes Hydroxy, R5 Alkyl, Cycloalkyl, Arylniederalkyl oder Aryl, und R6 substituiertes Amino oder substituiertes Hydroxy darstellen, und Salze von solchen Verbindungen mit salzbildenden Gruppen hemmen die blutdrucksteigernde Wirkung des Enzyms Renin und können als Antihypertensiva verwendet werden.

  式中的化合物 其中 R 是氢或酰基，X 是任选 N-烷基化的氨基酸残基，其 N-端与 R 相连，C-端与 X2 相连，X2 是任选 N-烷基化的氨基酸残基，其 N-端与 X 相连，C-端与基团 NR2- 相连，R2 是氢或低级烷基，R3 是氢、烷基、环烷基、芳基-低级烷基或芳基，R4 是羟基或醚化或酯化羟基，R5 是烷基、环烷基、芳基-低级烷基或芳基、R4为羟基或醚化或酯化羟基，R5为烷基、环烷基、芳基-低级烷基或芳基，R6为取代氨基或取代羟基，此类化合物的盐与成盐基团可抑制肾素酶的降压作用，可用作降压药。
• 5-Amino-4-Hydroxyvalerylderivate, als Zwischenprodukte in der Herstellung von Renin-Hemmern benutzbar
  申请人：CIBA-GEIGY AG

  公开号：EP0400290A1

  公开（公告）日：1990-12-05

  Verbindungen der Formel worin R3 Wasserstoff, Alkyl, Cycloalkyl, Arylniederalkyl oder Aryl, R4 Hydroxy oder veräthertes oder verestertes Hydroxy, R5 Alkyl, Cycloalkyl, Arylniederalkyl oder Aryl und R6 substituiertes Amino oder substituiertes Hydroxy darstellen, und Salze von solchen Verbindungen sind Zwischenprodukte zur Herstellung von Renininhibitoren.

  式中的化合物 其中 R3 为氢、烷基、环烷基、芳基-低级烷基或芳基，R4 为羟基或醚化或酯化羟基，R5 为烷基、环烷基、芳基-低级烷基或芳基，R6 为取代氨基或取代羟基，此类化合物及其盐类是制备肾素抑制剂的中间体。